Salonitenolide

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 461728

CAS#: 26931-94-2

Description: Salonitenolide is a germacranolide isolated from from Aegialophila pumila Jus. Boiss.


Chemical Structure

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Salonitenolide
CAS# 26931-94-2

Theoretical Analysis

MedKoo Cat#: 461728
Name: Salonitenolide
CAS#: 26931-94-2
Chemical Formula: C15H20O4
Exact Mass: 264.1362
Molecular Weight: 264.32
Elemental Analysis: C, 68.16; H, 7.63; O, 24.21

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Salonitenolide;

IUPAC/Chemical Name: (3aR,4S,6E,10Z,11aR)-4-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one

InChi Key: BLDTUWFMPJJRPR-PNQYDXICSA-N

InChi Code: InChI=1S/C15H20O4/c1-9-4-3-5-11(8-16)7-13-14(12(17)6-9)10(2)15(18)19-13/h4,7,12-14,16-17H,2-3,5-6,8H2,1H3/b9-4+,11-7-/t12-,13+,14+/m0/s1

SMILES Code: O=C(O[C@@]1([H])[C@@]2([H])[C@@H](O)C/C(C)=C/CC/C(CO)=C/1)C2=C

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 264.32 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Rosselli S, Maggio AM, Raccuglia RA, Morris-Natschke SL, Bastow KF, Lee KH, Bruno M. Acid rearrangment of epoxy-germacranolides and absolute configuration of 1beta,10alpha-epoxy-salonitenolide. Nat Prod Commun. 2010 May;5(5):675-80. PubMed PMID: 20521529.

2: Trendafilova A, Jadranin M, Gorgorov R, Stanilova M. Bioactive Compounds in Wild, In vitro Obtained, Ex vitro Adapted, and Acclimated Plants of Centaurea davidovii (Asteraceae). Nat Prod Commun. 2015 Jun;10(6):839-41. PubMed PMID: 26197494.

3: Esposito A, Malafronte N, Sanogo R, D'Ambola M, Severino L. Sesquiterpene Lactones from Vernonia nigritiana. Nat Prod Commun. 2016 May;11(5):583-4. PubMed PMID: 27319122.

4: Milošević Ifantis T, Solujić S, Pavlović-Muratspahić D, Skaltsa H. Secondary metabolites from the aerial parts of Centaurea pannonica (Heuff.) Simonk. from Serbia and their chemotaxonomic importance. Phytochemistry. 2013 Oct;94:159-70. doi: 10.1016/j.phytochem.2013.05.014. Epub 2013 Jul 1. PubMed PMID: 23827325.

5: Vanhaelen-Fastré R, Vanhaelen M. [Presence of salonitenolide in Cnicus benedictus (author's transl)]. Planta Med. 1974 Dec;26(4):375-9. French. PubMed PMID: 4465820.

6: El-Masry S, Vuilhorgne M, Evans FJ. Sesquiterpene Lactones from Aegialophila pumila. Planta Med. 1984 Feb;50(1):115. PubMed PMID: 17340274.

7: Bruno M, Rosselli S, Maggio A, Raccuglia RA, Napolitano F, Senatore F. Antibacterial evaluation of cnicin and some natural and semisynthetic analogues. Planta Med. 2003 Mar;69(3):277-81. PubMed PMID: 12677537.

8: Barrero AF, Oltra JE, Raslan DS, Saude DA. Microbial transformation of sesquiterpene lactones by the fungi cunninghamella echinulata and rhizopus oryzae . J Nat Prod. 1999 May;62(5):726-9. PubMed PMID: 10346955.

9: Zidorn C, Ellmerer-Müller EP, Dobner MJ, Stuppner H. A highly substituted germacranolide from Leontodon cichoraceus. Z Naturforsch C. 2001 Sep-Oct;56(9-10):904-8. PubMed PMID: 11724404.

10: Barrero AF, Oltra JE, Alvarez M, Raslan DS, Saúde DA, Akssira M. New sources and antifungal activity of sesquiterpene lactones. Fitoterapia. 2000 Feb;71(1):60-4. PubMed PMID: 11449472.

11: Huneck S, Jakupovic J, Schuster A. [Further Compounds from Centaurea stoebe.]. Planta Med. 1986 Oct;(5):398-9. German. PubMed PMID: 17345351.

12: Saroglou V, Karioti A, Demetzos C, Dimas K, Skaltsa H. Sesquiterpene lactones from Centaurea spinosa and their antibacterial and cytotoxic activities. J Nat Prod. 2005 Sep;68(9):1404-7. Erratum in: J Nat Prod. 2011 Sep 23;74(9):2029. PubMed PMID: 16180824.

13: Álvarez-Calero JM, Ruiz E, López-Pérez JL, Jaraíz M, Rubio JE, Jorge ZD, Suárez M, Massanet GM. 15-Hydroxygermacranolides as Sources of Structural Diversity: Synthesis of Sesquiterpene Lactones by Cyclization and Rearrangement Reactions. Experimental and DFT Study. J Org Chem. 2018 May 18;83(10):5480-5495. doi: 10.1021/acs.joc.8b00407. Epub 2018 May 3. PubMed PMID: 29694044.